Prior to 1958, the last defense of the America’s Cup had been in 1937, by the J-Class yacht Ranger, owned by Harold S. “Mike” Vanderbilt. The J-Class rules prescribing a vessel of some 120 feet in length were promoted by Vanderbilt and others for the defense planned for 1958, but economic concerns and the desire among aspiring competitors to employ smaller dual-purpose yachts won the day. The New York Yacht Club settled on the twelve-meter class rules, reducing the length of the average vessel to around sixty-five feet. Harry Sears, then the club’s commodore, formed a syndicate to build the ship and asked Briggs to join to help with finances.

Although building and racing his cars had long been Briggs’ primary field of endeavor, he had never stopped sailing, and he agreed to join the effort. Sailing legend Cornelius Shields was appointed as the team’s skipper but, when he suffered a heart attack, Sears asked Cunningham to take Shields’ place.

As a member of five East Coast yacht clubs, with almost thirty years’ experience racing several different classes of vessel, Briggs was a solid choice to lead. The one thing he lacked was experience with the starting strategy required by the head-to-head style of America’s Cup competition. Shields, a master of this type of racing, was happy to impart his knowledge to Cunningham, who proved an able student.

Unfortunately, as skipper it was Briggs who had to inform Shields that he could not remain a member of the crew; if he suffered an attack during competition and had to be taken to the hospital, it would leave them a man short and result in their disqualification. It was a tough moment for both men, but it was also characteristic of both to do what was best for the team.

The eliminations for the American side would prove to be more exciting than the final races. Four twelve-metre yachts, Easterner, Weatherly, Vim and Columbia, survived two months of run-offs to compete in the final eight-day round of match races to determine the defender of the America’s Cup. Of the four contenders, only the Vim had raced previously, but the nineteen-year-old vessel was so completely refitted as to be virtually brand new. The Easterner and Weatherly had been hurriedly completed and neither was fully prepared to compete, although the Weatherly would successfully defend the Cup in 1962.

Columbia benefited from a strong syndicate whose membership included Harry Sears, Olin Stephens, the designer of the Vim, and Cornelius Shields, Jr., who occasionally spelled Briggs as skipper. The competition finally narrowed to Vim and Columbia, which prevailed by virtue of her ability to better handle rough seas and strong winds.

The British challenger, Sceptre, entered by the Royal Yacht Squadron and skippered by Graham Mann, was a quite rotund 68,000 pounds compared to the svelte Columbia at 57,000 pounds, and the event was decided in four straight wins by the Americans.

During the post-race celebrations, Briggs located a pay phone and called Alfred Momo at Watkins Glen, where Ed Crawford had just won the main race. As Briggs was returning to join his crew, a reporter approached and commented, “Briggs, that was a fine race!” to which Briggs, still with the Glen on his mind, replied, “That’s what I just heard. I wish I could have seen it.”